Red Sox on the prowl before player market gets busy

Thursday

Nov 26, 2009 at 12:01 AMNov 26, 2009 at 2:53 PM

Sox GM Theo Epstein’s history is to deal before winter meetings and he has his eyes on ace Roy Halladay

Mike Fine

The perception of the annual MLB winter meetings is that it’s a free-for-all meat market of free agents replete with clandestine meetings in shady corners between general managers and agents, and wholesale sell jobs by those agents.

True, but the league’s GMs would much prefer to avoid the clamor and make their deals well before the meetings commence. The Red Sox have been fairly successful in doing just that during the Theo Epstein regime, making numerous deals before the meetings, which this year begin on Dec. 7.

(Epstein made this year’s first move on Thanksgiving Eve, acquiring infielder Tug Hulett from the Royals. Hold the applause.)

Epstein’s first coup, in fact, was the signing of Curt Schilling. Six years ago he was sitting in Schilling’s dining room partaking in the Thanksgiving dinner that led to the Schilling acquisition, thereby keeping him away from the Yankees and any other vultures who’d be awaiting him as the meetings loomed. Schilling told WEEI listeners on Wednesday that while the Sox were visiting, he took an illicit call from the Yankees in another room.

At Thanksgiving time two years later, Epstein had resigned from his post with the Sox, part of a power struggle with CEO Larry Lucchino at the time. It’s still widely believed that Epstein had a hand in the second huge pre-meetings deal that would affect the Sox for years to come. In this case, acting associate GMs Jed Hoyer and Ben Cherington completed the swap of Hanley Ramirez, Anibal Sanchez, Harvey Garcia, and Jesus Delgado for Josh Beckett, Guillermo Mota, and Mike Lowell. Two years later, on Nov. 20, 2007, the Sox nailed down Lowell for a three-year extension, which seemed like good work at the time.

Last year at this time the Sox acquired reliever Ramon Ramirez from the Royals in exchange for Coco Crisp.

Aside from dozens of minor additions and deletions, the Sox continued to be busy throughout the last six years leading up to the winter meetings, or at least before the end of the year.

They signed Keith Foulke, for instance, on Dec. 13, 2003, complementing their Schilling deal. On Dec. 9 a year later they signed David Wells and a few days later, Edgar Renteria and Matt Clement.

On Dec. 7, 2005, they acquired Mark Loretta and a day after that Andy Marte from Atlanta for the ineffective Renteria. In ’06, between Thanksgiving and the meetings, they signed both Julio Lugo and Hideki Okajima.

Not all of the deals worked out, of course, but they were big signings at the time, alleviating much of the pressure of having to deal during the meetings or heading into the following year as spring training approached.

This year, the stakes are much higher. This year the Sox have one of the best starting pitching staffs in the majors, and have an opportunity to add one of the best pitchers in the majors, Roy Halladay. They’re also faced with doubts about third baseman Lowell’s hip, David Ortiz’s continuing decline as the DH and Jason Bay’s free agency, leaving a void in left field.

The Sox on Wednesday continued their sincere pursuit of Halladay, hoping to make a deal with the Toronto Blue Jays, who wouldn’t part with their prized right-hander, a former Cy Young Award winner and six-time All-Star with the 148-76 career record.

Epstein is attempting to keep from losing two prized youngsters, Clay Buchholz and Casey Kelley, both right-handers, in a Halladay deal.

The New York Daily News quotes unnamed sources as saying the Red Sox are putting on a “full-court press” in their efforts to obtain Halladay. JP Ricciardi, the GM who would not part with Halladay at the trading deadline last summer, has been replaced by Alex Anthopoulos, who says a trade could be made, even within the division, if it benefits his club.

The question remains, should the Red Sox part with young prospects such as Buchholz and Kelley for a soon-to-be 33-year-old with 12 successful but hard years behind him?

History would say yes. There was an argument about obtaining the veteran Schilling, who was 37 with 16 full big-league seasons behind him when obtained by the Sox. Schilling went on to win a league-high 21 games in the 2004 championship season, which overshadowed the three hard years that were to come. The youngster some didn’t want to give up, Casey Fossum, went 4-15, 6.65 for Arizona that year and has gone 26-42 since leaving the Sox. He was a member of three organizations last season and pitched three major league innings.

The Red Sox, with their resources, are able to use youngsters as bargaining chips and sign high-priced, quality free agent pitchers. It’s been a continuing theme over Epstein’s six seasons. With a starting staff of Beckett, Jon Lester, Daisuke Matsuzaka, and Tim Wakefield, there’s certainly room for Halladay, even if Buchholz can be retained.

Wakefield remains the X factor, having been unable to finish the last two seasons because of injuries. That makes the acquisition of another major pitcher even more critical, but what do the Sox do if Halladay is not obtainable? There are others out there, but not nearly as prized: John Lackey is an Angels free agent who will come at a price, but he doesn’t have Halladay’s pedigree. Erik Bedard, Rich Harden, Ben Sheets, Justin Duchscherer and even Pedro Martinez are available, but there are extenuating circumstances with each of them.

Halladay, though, is the cream of the crop, and the Sox would like to think the cream rises to the top.

Mike Fine may be reached at mikefine@ledger.com.

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